I Never Stood A Chance

Story Info
Given an inch, Jen takes a mile and more.
4.4k words
4.46
14.3k
17
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"What? Jen, what are you doing? This is my bed! Why are you here? Jen, stop that! Jen, stop it! What the hell? Oh, for Heaven's sake, Jen, you're naked! Uhmm, stop doing that! Stop touching me -- uhmm -- and kissing me!"

"Uhmm, why, Conrad?"

"Because you're my student aide -- and -- young enough to be my daughter! Uhmm, will you stop kissing me, Jen! And...uhmm..."

"Conrad, right now we're not at the college or at work -- uhmm -- and I'm definitely not your daughter -- uhmm -- and I like kissing you..."

Despite my feebly uttered protests, I had to admit that I found Jen's soft lips and sweet mouth were indescribably enticing. And her tongue, oh, my god, was doing one hell of a job in my mouth -- electrifying and overloading it like never before. But somehow -- this just wasn't right.

"Jen," I gasped as I finally managed to break away from her delicious lips in a desperate last-ditch-attempt to stop what was happening, "If we get caught and people find out... Jen, don't go down there! Oohh, please stop that. Stop kissing me. People will think I took advantage of you -- uhmm...uhmm..."

Jen muffled my lame protest with kisses that grew increasingly passionate, urgent, and demanding. Then shifting her soft youthful nudity on top of mine, she casually rubbed her stark nakedness against me as she drove me absolutely crazy with kisses to my face and neck.

"We won't get caught, silly. No one will know...uhmm," Jen mumbled between planting hot kisses and licks on me, "and if anything...I'm the one who's taking advantage of you. Oooh, what's this long, hard 'thing' in your boxers?"

Jeez, was Jen right? I had a humungous boner -- the likes of which I hadn't had in years. This sweet, innocent-looking Asian girl -- no, woman -- a very "young" pretty woman who looked more like a petite teenager than a twenty-one-year-old woman. With twinkling eyes, a cute giggle, and pretty in a girl-next-door type of way, her youthful figure had modest hips, tight buns, and nice legs. Her breasts were small enough that she didn't wear her a bra...something that she did often...opting to wear a chemise instead.

Yet, as I involuntarily responded to her kisses and touches, I realized that somehow Jen had amazingly stimulated me in ways long forgotten. How long had it been since my last girlfriend or for that matter when I last had sex? Shit, I couldn't remember when this "confirmed bachelor" had felt so good...so goddamn alive!

Straddling my hips, Jen squirmed on top of me. Her every movement teasingly brought the slick wetness of her womanhood between her inner thighs in touch with my boxer-covered raging manhood. Jen was clearly an irresistible erotic force who was shamelessly rubbing her naked petite form against me, shattering and crushing what weak resistance that I may have had left.

"Jen, please stop," I pleaded as I felt my toes hanging over the proverbial crumbling cliff edge of idiotic self-denial and raging desire. "You don't have to do this! I'm not asking you to do this..."

"That's why I am doing it, Conrad! Uhmm, how I love the way you kiss back," Jan whispered between kisses. "This is my way...uhmm...of thanking you for taking me in...uhmm... when my ass-wipe of a former boyfriend kicked me out of his place. Uhmm...and when my parents wouldn't take me back...uhmm. I had no place to go and no one to turn to... uhmm...you were there for me...even though you didn't have to."

"Jen, I didn't help you to have sex with you." That was the truth. Although with a lot of trepidation, I help a despondent and alone Jen. As I saw it, she was a nice kid, cute and shy, who was just down on her luck. It was only after my act of kindness that I came to realize just how lonely I was. For when Jen moved in, she filled the house with airy lightness and subtle warmth that only a woman can -- albeit a very young attractive woman. "I wouldn't take advantage of you like that."

"Conrad...uhmm...you took me in...gave me my own bedroom... uhmm...gave me my own space...fed me, and even bought me clothes and things that I needed. You took care of me and never once hit on me -- never once asked anything of me -- even though I would have done anything -- uhmm -- you wanted.

"I know that you would have never asked, so I decided to take matters into my hands. I know that I don't have to, Conrad, but I really want to..."

Somehow while distracting me with her kisses and caresses, Jen had managed to pull down my underwear to release my aching cock. I gasped loudly as Jen's petite hand slide between her legs and her slender fingers wrapped around my shaft.

"Oh, see how nice and hard you are," Jen moaned as she straddled my hips and squirmed sensuously as she rubbed my flanged head up and down her swollen slippery slit. "Oh my god," Jen murmured dreamily, "I never would have thought you were 'this' big."

Although I protested in vain (albeit somewhat weakly), Jen pushed back and down, and before I knew it, embedded me firmly into one of the tightest pussies I had ever experienced. I had always thought that it was an urban myth that Asian women are naturally tight due to their diminutive bodies. But as Jen's molten velvet wetness that gripped and milked me, I quickly change my opinion. She was so goddamn tight that if I hadn't known that Jen had quite sexually active with her previous boyfriends, I'd swore she was a damn virgin.

"You're so...big," Jen winced, her almond eyes pressed tightly shut. With her nostrils flaring, she winced, moaned, and lay on my beating chest. "Oh, don't move. Hold still, Conrad. Let me get used to you. I'm being penetrated and stretched like never been before. Oooh, damn it, you feel so damn good!"

Then lifting her chest from mine, Jen began to slowly rock back and forth. Soon her stiff pink pencil-erasers nipple extended fully from her perky small boobs. Beads of sweat dripped from Jen's delicate face, then ran down her ivory neck before dripping from her rosy tips. Her long chestnut hair that had swayed with her every movement, now clung to her glistening skin as my swollen cock began to sink steadily into her tight cunt.

"Oh, my god, Conrad, I can feel myself throbbing around you. I never knew it could be so good," mewled Jen in a girlish tone. With her small slanted eyes pressed shut, she slowly began to gyrate her hips, undulating as she pushed back until her sparse pubic hair mashed and rubbed against mine. "I can't believe it! I took you all the way up my little cunny!"

Now all this really made me feel like a dirty old man -- a very "horny" dirty old man with this Japanese-American Lolita who was skewered on the end of my fleshy spear. I had been seduced by Jen's youthful body and wanton enticement, and I willingly and completely surrendered to her and my raging bestial urge to rut.

My hip began to lift, taking her with short quick but powerful thrusts, and Jen gripped my shoulders tightly as she was tossed like a rag doll. Whimpering to each stroke, she whined, "Oh, Conrad, you're filling me up like never before -- and believe me when I say that I've had my fair share of boyfriends. But, oh my god, I never had one like you. Can you hear how squishy wet I am? Ooh, yeah, you're churning my pussy juices. You're going so deep and making me so hot and horny. I'm burning up -- ooh, I'm such a damn slut!"

Her small breasts quivered enticingly with each thrust and her pink nipples that jutted from puffy cherry-blossom areolas danced before my lust-filled eyes. Lifting my head, I greedily inhaled a tender mound, sucking in as much as could before letting it slip from my sucking lips. My lashing tongue and nipping teeth soon had her nipple so hard that it could cut diamonds.

A loud groan came from Jen's panting mouth when I finally released her tit only to be followed by a sharp gasp when my mouth engulfed her other small breast. "Oh, yes - ohh, please -- mouth my sensitive little titties," Jen droned as she shoved a tender mound into my mouth. "Make my nippies stiff and achy! Yeah, just like that! Suck my nipples, Conrad, suck then hard!"

Jen suddenly squealed in surprise when my finger that was well-lubricated in her pussy juices was pressed into her puckered asshole. I couldn't help myself since I had always wanted to screw a woman's behind but never could find one willing to let me. Even though I expected her to protest and wiggle madly to remove my digital intrusion, I still couldn't resist Jen's inviting little anal orifice.

It was, however, my turn to be surprised as Jen pushed back, her back arching, to drive my embedded finger deep into her spasming rectum. Shaking uncontrollably, Jen ground her cunt against me before breathlessly uttering with a sigh of undisguised lust, "Oooh, how did you know, Conrad? How did you know that I love taking a man's cock back there?"

Jen twitched her buns and her anus squeezed my probing finger. "But, right now -- I want your big fat cock that's filling my pussy. I want to feel your hot sticky white cum spurting into me and then oozing out me to run down my legs. Fuck! I'm so close to coming! Yeah, oh yeah, I'm going to come soon. Ooh, shit, I'm so fucking close," Jen whined, her voice hot and ragged.

Grabbing and squeezing her tight buns, I began to ram between her splayed legs with long, powerful strokes. My nuts were so tight that they ached but I struggled to delay my release so that I could last longer.

"Oh. give it to me, Conrad, give it to me now!" With that said, Jen humped my embedded cock hard madly, feverishly grinding her fleshy sex against mine. She shook uncontrollably as her hair flayed about as she cried out in a shrill voice, "Oh, shit! I want to come so badly! Goddamn it! Fuck my twat hard, Conrad! Don't stop, damn you!"

"Arrgh! Arrgghh!! Arrrggghhh!!!"were our mingled guttural grunts as my nuts burst with molten lava into the depths of her twisting body and triggering Jen's tiny twat bursting with a sudden tsunami of wetness.

Jen collapsed as a sweat-drenched twitching heap on me, panting breathlessly as she clung to me. "Conrad," whispered Jen after she regained her breath, "I know that you're going to say that what just happened is wrong because I am some twenty-five years younger than you. But I wanted to...and boy, am I glad that I did it. Now, Conrad, don't say anything -- just shut up and enjoy my repayment in kind."

And you know what? Jen's right and I did.

~ ~ ~ ~ ~

Since seducing me, Jen made sure to become an integral part of my life despite our seemingly overwhelming age difference. Under her loving and youthful care, my masculinity has received a kick-start and my middle-aged body has been transformed into rampaging hormones and unexpected rock-hard erections.

Like tonight when we were on the couch watching television before going to bed. Snuggling up to me, Jen slyly slips her small hand into my underwear. Then slowly and gently stroking me, she stroked me until I grew rock hard in the pumping ring of her thumb and forefinger. When I finally asked what she was doing, Jen kissed me on the neck before snuggling up to me to whine in that little girl voice of hers, "Conrad, I'm horny...really horny... and I need you...now..."

I don't know how she did it but the next thing I knew Jen slipped off the couch and in so doing, pulled my boxers off to free my rigid manhood. Then quickly shucking her baggy sleep t-shirt, she knelt nude between my widespread legs, and teasingly licked my throbbing shaft and tightening balls. The tip of her cute darting tongue teasingly probed the slit of my head before my flanged head disappeared between her deliciously parted lips, then with practiced ease, Jen bobbed her head to repeatedly took me deep down her throat.

Then in keeping with the surprises of the night, Jen produced a tube of KY jelly

and proceeded to give my throbbing penis a thick coat before applying a liberal amount to her nether region. With an impish smile on her face, Jen quickly slid up my body until she knelt to straddle my hips. Leaning against me, she reached between her legs to guide my swaying trouser snake to an inviting burrow of her young body. However, it soon became apparent that I was knocking not on her front door but rather her rear entrance.

After one hell of a breathtaking kiss, Jen whispered in my ear as she continued to gently wiggle and wormed my dickhead against her inviting anal puckered, "Conrad, I'm really, really horny." Whimpering in that endearing girlish tone that she knew turned me on, "Please don't think badly of me but I've got this terrible itch between my buns that needs to be scratched! Will you please butt-fuck me? I want to feel this beautiful cock of yours spread my butt cheeks and after being shoved up my asshole, scratch my butt-itch. Do you want to sodomize me, Conrad?"

When I grinned widely and nodded my head vigorously, "Goody! Now, you just lay there and let me do all the work." Holding my dick with her little fingers, Jen took a deep breath and then letting it out slowly, sat down on my fleshy stake. "Oh my god, I can't believe it. Even though I lubricated you really well...and have been buggered so many times...it was a bitch getting your fricking thick dick into my snug little asshole. Thank god that I wanted you so badly, but, it sure was an eye-opener it was when your dick finally popped through my anal ring.

"Oh Conrad, "you're so goddamn big! please don't move," Jen panted hotly. "I can't believe how your big fat prick fills me up -- making me want -- no, need -- to have all of my old man's dick shoved up my asshole and spreading me out!" Then gingerly wiggling her buns, Jen whimpered pitifully as she gradually worked me raging hard-on through her tightly stretched anus and further into her sizzling rectum. "Ooh, yeah, just like this..."

With that said, Jen began to slowly ride me, taking more of me with each downward thrust of her hips. With her almond-shaped eyes pressed shut in utter bliss and her delicious mouth open to emit short breathless gasps as I thrust upwards to meet her downward push.

"Oh, yeah, yes, just like that!" moaned Jen "It feels so damn good, having you sliding in and out of my hot asshole. Don't stop roto-rootering me...oooh, don't stop! Cum for me, Conrad...cum in me...fill me up! I want you to shoot you load up my ass, Conrad! I've been so slutty...so very naughty. Please, don't make me beg, baby! Make me your little whore, Conrad -- please!"

That was all I needed as the sperm from my tightened nuts suddenly erupted deep into her squirming bowels. This sent Jen squirming and wiggling madly as she lifted herself up, quivering my shaft. Jen then exploded in an uncontrolled frenzy that had her wildly grinding her sex against me as she humped herself into a massive orgasm.

After what seemed like hours, her sweat-covered body collapsed limply on mine as spasms of her fading climax still ran up and down her spine. "God...I love it...when I climax... with your cock...crammed up my asshole," Jen panted breathlessly as she lightly kissed me. Then after a soft chuckle as she sprawled on me, Jen whispered, "Oooh, you've stretched me out so badly that I don't know if I'll walk properly...for the next few days.

"Do you know that you were an absolute beast of an ass-reamer...the best that I ever had...and like I've said before, I've had quite a few. It seems that men just can't resist porking my little butt, especially if they know that I'll let them. The only problem is that instead of going slow and easy, most just want to ram it in. When my first boyfriend cracked my cherry ass, it hurt so much that I wanted to curl up and die. But he didn't care. He just kept screwing my asshole and with each time, I got used to it. I mean he really wanted it so badly, and I figured why not? And it got easier and eventually... well..."

When I mentioned that we didn't have to do anal sex, Jen just wiggled her slender hips and squeezed my still throbbing prick buried in her ass. "I know, but sodomizing me has been something that you always wanted to do...your special fantasy. That's why I had to have you ass-ream me. I love how you buggered me. I love you, Conrad."

With that Jen slipped off of my lap, my semi-soft cock sliding out of her anal orifice with a lewd slurping sound. Before I could ask her what she was doing, she pressed me back on the couch and took me into her small mouth to leisurely slurp my slime-coated cock and balls.

I pulled Jen to me and spun her small body on top of my torso with my face between her legs in a classic sixty-nine position. Yet, when spread her small tight buns, my eyes were immediately drawn to her quarter-size dilated rectum that oozed with my recently deposited milky-white spunk. After admiring my handiwork, I buried my face in the fork of her legs and let my tongue snake into her love slit and lapped up her slippery love juices. My tongue tip then drilled into her sweet pussy hole was before burrowed into her squirming anus. Jen's writhing became so violent that I had to wrap my arms around her thighs, allowing my hands to clutch and spread her spongy buns for deeper tongue-fucking penetration.

Finally breaking free of my grasp, Jen twisted about, her mouth landing on mine as she kissed me silly. "Oooh, you're a nasty old man," she panted as she kissed me again, "Now see what you've done. You've made me all hot and bothered again, and I've got only one hole left that hasn't been used and needs to be satisfied."

With that Jen grabbed my semi-hard manhood and quickly shoved me into her welcoming cunt. "Oooh," Jen moaned as she rode me, bumping and grinding wildly against me, "I hope you've happy...as much as I am. Oooh, I love you, Conrad, you dirty old man. I want to keep on living with you and being you little fuck-slut. Don't fight it because in the end, I'll win and you'll enjoy every moment."

~ ~ ~ ~ ~

Almost a year has passed since I took in Jen, my student employee who in her final semester of college, and who took over a much older confirmed bachelor's life and made it hers. How Jen managed to finish her college studies given how often she constantly jumped my boner, I'll never know. I just know that she did it.

People eventually discovered that Jen was living at my house, but they also knew that she was down-and-out when I took her in. While there was some speculation about us, it was so incongruous that a cute young thing like Jen and an old fart like me would click much less doing the naked horizontal mambo in bed. As such, rumors about us were dismissed by many.

After receiving her degree, Jen quickly got an entry-level marketing position with a medium-size production firm. While the job paid enough for Jen to make ends meet and contribute to the household, there wasn't enough for her to move out -- not that she was inclined to do so (nor was I willing to let her go). Jen, however, went about making my house into our home, and I had to admit that the place looked refreshed the place. But, while I appreciated her house improvements, having a naked young Asian woman snuggling up to me in bed was the best home improvement of all time.

While it should not have come as a surprise, Yet, Jen let me know in the middle of a mind-blowing blow-job on the eve of our first anniversary, "Conrad, I've gotten off the pill. Why? Because I wanted to have your child." The thought that Jen wasn't on birth control and the possibility of me being a father at my advance age was a splash of icy water of reality, enough to deflate my erection.

But Jen would have none of this and with practiced use of her mouth and hand, kept me rigidly hard. "Honey, I love you and know that you love me. I want to be a permanent part of your life, and to me, this means having your child. You don't have to marry me if you don't want to...all I asked is that you provide for our child...or children. What's that? If you knock me up, you'll marry me? What a better inducement to get preggie."

12